The 50 Greatest Alternative Hip-Hop Albums of All Time

The answer to that is pretty simple: alternative hip-hop is a silly distinction developed by music writers to help compartmentalize a diverse genre in a way that's easy for them to apply. But, cynicism notwithstanding, the term has merit and the subgenre has a lengthy history that sometimes goes under-acknowledged.

Alternative music tends to be music that goes against the conventions or the mainstream standards of a particular genre. From the Velvet Underground to Janelle Monae, there have always been artists who seek to define themselves and their art in a way that sets them apart from what fans and critics come to expect of their respective genres. Most genres enjoy a period where that kind of unbridled creativity is embraced by the most visible platforms; but unfortunately, that kind of visibility tends to disappear once said genre starts to enjoy major commercial viability.

In the early 1990s, “alternative hip-hop” was marketed as the music of esoteric and pretentious quasi-hip-hop acts like P.M. Dawn and Me Phi Me. This isn’t what we’re celebrating here. This isn’t “alternative” as defined by non-rap writers looking to find music that speaks to their tastes. This is alternative music as defined by lovers of hip-hop. And while artists like Kanye West and Eminem have certainly been visionary; they haven't consistently flown in the face of the genre's norms in the way that these 50 albums have.

So we at The BoomBox have decided to celebrate 50 albums from throughout hip-hop’s history that have defied convention and cliché; albums that represent what we consider the dual side of “alternative hip-hop:” one side devoted to an “artsy” aesthetic and earthy approach; and the other side devoted to just being straight-up odd and unconventional. Both represent a necessary alternative to what can be the monotony of the mainstream. To be sure, this is not an anti-mainstream list, some of these albums were actually very popular. From OutKast to MF Doom, this is a list of albums that celebrate individuality in what can sometimes be a sea of conformists.